Heretofore tertiary amines have been prepared in a wide variety of reactions utilizing various metal-containing compounds as catalysts. For example, U.S. Pat. No. 3,091,641 discloses a process for preparing tertiary amines in which a secondary amine and an aliphatic ketone are reacted with carbon monoxide and water in the presence of an iron carbonyl catalyst such as iron pentacarbonyl or biscyclopentadienyl diiron tetracarbonyl. Another U.S. Patent, namely, U.S. Pat. No. 2,497,310 discloses the synthesis of amines in which an unsaturated compound, carbon monoxide, hydrogen and ammonia or a substitute ammonia are reacted in the presence of a cobalt catalyst although other catalysts which possess hydrogenation properties such as nickel, ruthenium, iron and copper may also be used. Another prior art reference, namely U.S. Pat. No. 3,947,458 is drawn to a process for preparing amines in which nitrogen-containing compounds and an olefin along with carbon monoxide and water are reacted in the presence of a catalyst comprising iron pentacarbonyl and a rhodium compound. In like manner, U.S. Pat. No. 3,234,283 also discloses a process for the preparation of trialkyl amines in which an olefin is reacted with carbon monoxide, hydrogen and a dialkyl amine in the presence of a catalyst consisting essentially of cobalt carbonyl trihydrocarbonphosphene. The hydrocarbon content of the catalyst is limited to trihydrocarbons containing a total of up to about 30 carbon atoms, the number of carbon atoms in any one of said hydrocarbon radicals not exceeding 18. Other prior art patents include U.S. Pat. No. 3,758,586 in which ethylene is reacted with secondary aliphatic amines in the presence of rhodium or iridium catalysts to form a tertiary amine in which one of the substituents is, of necessity, ethylene; U.S. Pat. No. 3,513,200 in which the preparation of tertiary amines is accomplished by reacting a secondary amine containing from 2 to about 20 carbon atoms with an aliphatic hydrocarbon olefin containing from about 2 to about 20 carbon atoms, as well as carbon monoxide and hydrogen in the presence of a complex catalyst comprising a Group VIII noble metal hydride in complex with a biphyllic ligand, said ligand containing phosphoric, arsenic or antimony; U.S. Pat. No. 3,412,158 which is drawn to a process for the preparation of aliphatic amines from the reaction of lower molecular weight olefins and ammonia, the primary product comprising a primary amine rather than a tertiary amine; U.S. Pat. No. 2,501,509 which is drawn to the preparation of amines by heating an ammonia type compound with a hydrocarbon olefinic compound utilizing an alkali metal catalyst such as sodium, this reference requires the presence of an organic liquid diluent for the olefinic reactant; and U.S. Pat. No. 2,422,631 in which aliphatic amines are produced by reacting an olefin, an oxide of carbon, hydrogen and an aminating agent in the presence of a hydrogenation-dehydration catalyst, examples of these catalysts being zinc chromate, zinc tungstate, chromium phosphate, cobalt oxide, iron oxide, etc.
In contradistinction to the above reactions, it will be hereinafter shown in greater detail that tertiary amines may be synthesized by utilizing a particular rhodium- or ruthenium-containing catalyst to obtain an economically attractive conversion of the olefin compound with an economically attractive selectivity to the desired product.